Love With A Stripper
by littlewankershim
Summary: Santana is a bratty rich girl with more money then she knows what to do with. Being a closeted lesbian doesn't help her score with the ladies. One night at her brother's bachelor party she meets a stripper who's caught her eye. Drunkenly she offers the woman 500 to sleep with her, however what happens next Santana didn't see coming. This is a GKM fill
1. Chapter 1

**Love with a Stripper**

**Prompt Summery:**

Santana is a bratty rich girl with more money then she knows what to do with. Being a closeted lesbian doesn't help her score with the ladies. One night at her brother's bachelor party she meets a stripper who's caught her eye. Drunkenly she offers the woman $500 to sleep with her, however what happens next Santana didn't see coming. This is a GKM fill

* * *

"Santana hurry up! Your brother's about to make a toast!" Alma Lopez shouted from the bottom of the marble staircase. Santana ignored her and fidgeted with her dress and make up one more time before feeling satisfied with the way she looked.

It was the night before her brother's wedding day and her entire family had gathered in a joint bachelor and bachelorette party hosted by her father. Their bell-air mansion was packed with people and servants darting around and celebrating Juillian's last night as a single man. His soon to be wife Angelica and all of her guests sat by the jacuzzi while bulky men with arms the size of bowling balls rubbed body oil into their skin.

On the far side of the spacious back yard sat two separate stages. One for the dj and anyone interested in making a toast and another with three large poles where dancing girls stripped for a crowd of dancers.

"Santana where have you been!" her abuelita asked impatiently grabbing Santana by the hand and dragging her to the front of the first stage where her brother stood holding up a glass to silence the crowd.

"Good evening everyone. I hope you're enjoying this wonderful night of drinking an debauchery. I just wanted to say a quick thank you to all the wonderful people who have supported Angelica and I through the years, thank you to my papi for footing the bill for this huge party, and also to my amazing sister Santana. I hope you find a love like mine, baby sis. You deserve it." Jullian held up his glass and everyone cheered. Santana on the other hand shrunk any feeling embarrassed.

Santana very much doubted she would ever find a love like the half baked business arrangement between Jullian and Angelica. She had known from a very young age that the kind of love she longed for would be different then most everyone else's. Santana loved girls. She loved them in a special and forbidden way and nothing would change that.

"Excuse me abuela. I need to go grab a drink." Santana dismissed herself from the large group of people and made her way over to the bar ordering her third long island ice tea of the night. She tried to force herself to watch the thunder down under show through the living room window, but found the men who worked it dirty. She made a sour look and walked off to find something to entertain herself with.

Standing near the dj booth she was able to watch the strip show taking place on the second stage without looking strange for watching. A few older more sexually liberal women stood cheering right along side the men as a stunning blond dipped and teased the crowed with her sexy moves. Most of her clothes were still on half way through the dance, but it was the way she worked her body that made the show so erotically hypnotic to watch.

The lanky blonde dancer unbuttoned the black vest of her three piece tux reveling a tight white lace corset underneath that held her breasts practically up to her chin.

"Fuck." Santana groaned licking her dry lips as she watched the woman take a quick spin around the stripper pole while sending her tux pants flying out into the audience. The crowed whistled and threw tens and twenties up on the stage while Santana's head swam with the alcohol in her system. Another stripper joined her on stage wearing a more sexed up version of the tux the blonde had been wearing. They looked like the stripper version of the man and wife cake toping. Not waisting a single moment the blonde grabbed the other girl and brought her in for a sexy kiss unlike anything Santana had ever witnessed before. She could feel the hot arousal grow more intensely in her belly.

'Maybe she'd kiss me like that if I asked.' Santana thought blurry eyed.

"Hey Santana. Come here for a sec!" Jillian called from a few feet away. He stood in a small group of business men talking seriously with one another. Reluctant to leave her post Santana made her way over to see what he needed. "I'm really busy right now, but do you think you could go pay the strippers. Give them this. It should be enough to cover the night." He placed two hundred dollar bills in her hand and sent her on her way.

Santana swallowed her pride and marched off to find where the two girls had gone. Go-Go dancers had replaced them on stage and the party was starting to hit it's stride. Fifteen minutes later Santana finally cornered the second girl.

"Where's your friend?" Santana shouted over the loud music.

"I think she went to use the bathroom upstairs." the stripper replied sticking her hundred down deep into her bra along with the stash of tens and twenties she had earned for the night.

Santana thanked the girl before staggering her way through the crowd, drink still in hand. She eventually found the blonde stripper emerging from the upstairs master bedroom wearing a less then sexy set of sweat pants and hoodie, which caused Santana to pout endlessly.

"Why such a sad face cutie?" The blonde winked spotting Santana standing in the door way. Her tan cheeks turned a slight shade of red though she could feel the liquid bravery still coursing through her body.

"You changed clothes...I brought your money from my brother. You were amazing. I've never seen anyone dance like you" Santana grinned holding out the hundred for the woman to take. A closer look showed that she couldn't be that much older then Santana though clearly out of high school.

"You're sweet. Thank you." the woman giggled accepting the money with a cute smile that made Santana's heart flutter. 'Maybe she's into me?-oh yea. She's totally into me' said the belligerent devil on Santana's shoulder. The blonde woman moved to walk by, but Santana caught her by the arm.

"Wait—I was wondering if you wanted to go back to my room. I could pay you." Santana said unaware of how sleazy she actually sounded. It was the first time she had ever felt like a girl was flirting back with her and she didn't want to waste the opportunity to lose her virginity, especially to someone as hot as this girl.

"Excuse me, what did you say?" The woman cocked her head to the side with a mildly annoyed look on her face.

"Oh, sorry I didn't mean to upset you. It's just-I mean you're obviously here for the money. It's not like you're like you're actually here to pay for college or something like that. I think you're beautiful and-"

"You can stop right there. I think you have me mistaken for someone else. You're obviously drunk, so I'm going to go." The blonde growled in Santana's face yanking her arm away and storming off down the hall.

"Wait!" Santana called after her.

"What?!" The woman whirled around and glared. Santana picked up a pen from a small decorative table meant for taking notes while on the phone.

"You didn't let me finish." Santana took the woman's hand and scribbled out several digits. "You're really beautiful. If you change your mind about having sex with me I can pay you five hundred dollars. You might have not noticed, but money isn't exactly and object around here. Think about it. " Santana murmured and leaned against the wall droopy eyed. All the alcohol was slowly taking it's effect. She knew she'd regret it in the morning, but right now the only thing that mattered was the hot blonde stripper in front of her.

"Why don't you take your money and go fuck yourself with it." the woman snapped, took off down the stairs, and out the door.


	2. Chapter 2

Santana sat with her face pressed to the cool wood of her fourth period english desk as she tried to will away her massive hang over. The weekend was one big wedding blur ending with her brother boarding a plane to some private island in the Caribbean. Her best friend Quinn sat next to her squawking on and on about graduation and all the campus tours she had scheduled at the end of the month.

"Are you even listening to me Santana? I said I think you and I should check out UCLA together. Think about it. If we made the cheer team we would own that place. Not to mention all the social hook ups. You could study dance or whatever and I'll check out their business department."

Santana lifted her head and brushed her long dark hair out of her face.

"Sounds like a plan." she grimaced as her phone lit up with a notification for a text.

"How was the wedding? Did you meet anyone? Did you hook up with a stripper?" Quinn pried.

"Who said anything about strippers?" Santana shot back feeling her heart race.

"Angelica told me all about inviting the guys from Thunder Down Under. You were a part of the wedding party right? Don't bride's maids usually hook up with the hottest guys at the wedding? That's a thing right?"

Santana relaxed and opened her text.

"No, I didn't hook up with any of the strippers there. Who knows where they've been." She gave a fake shutter at the idea.

**Blocked: Is your offer still on the table?**

Santana re-read the message several times trying to recall if she had messaged anyone about buying weed recently.

**Santana : Who is this?**

"Santana your young. You need to get laid. Trust me I think you'd be a lot less-intense if you got some. Sure it kinda sucks the first time or two, but after that it's all great. Trust me you don't want to go to college with your V-Card still intact you know what I mean."

**Blocked: Brittany.**

**Santana: I think you have the wrong number I don't know a Brittany.**

**Blocked: We met the other night. I was a dancer at your brother's party...**

Santana felt her blood turn to ice. The stripper she had propositioned for sex had actually messaged her back. Santana had felt so guilty the next day for acting like such a rich tool to the poor woman who was just trying to make a living. She might have been a bitch, but she wasn't completely heartless.

"Sorry Quinn, I have to go." Santana grabbed her bag and excused herself to the bathroom.

'Fuck what do I say to her? Does she want to have sex with me? -don't be stupid she wants the five hundred you offered her. ' Santana thought as she stared at her reflection in the bathroom mirror, contemplating the options at hand. 'Quinn's right, I don't want to go to college a virgin and this could be my only chance to learn from someone who actually knows what she's doing.' it didn't hurt that Brittany was totally hot ether.

Santana pulled out her phone and replied.

**Santana: I remember now. Yes the offer is still on the table, if you're interested. $500 for one night with you.**

**Blocked: Good. Saturday night at 6pm. Find a place.**

**Santana: 6? I'm not sure that's going to work for me.**

**Blocked: You'll make it work or no deal.**

Santana swallowed a lump in her throat. She could hardly believe this was really happening.

**Santana: Okay, I'll make it work. We'll meet at my house.**

**Blocked: Fine. Have Cash.**

**Santana: Thank you.**

* * *

Santana paced around her mansion manically waiting for the clock to hit six. She wore a fine silk black dress with matching heals and a set of lingerie underneath freshly bought from Fredrick's. She must have replied her lush red lipstick at least twenty times while she waited.

Finally the doorbell rang and Santana thought she might pass out. The bell rang again and Santana shouted for one of her servants to hurry and get the door. When there was no reply and the bell rang a third time, Santana remembered she had sent everyone home for the night.

"Shit." Santana muttered practically running down the stairs in her Jimmy Choos to get the door.

"Hi ! Sorry ! I forgot that I sent everyone home." Santana shouted through the closed-door as she went to open it. Brittany on the other hand didn't seem nearly as amused.

"Do you keep all your guests waiting?" She said dryly taking a look around the giant house before letting her gem like blue eyes fall on Santana, whose heart was already racing.

"What—no! Of course not. Come in and make yourself at home." Santana said ushering the woman inside. There were few words that could fully describe Brittany in Santana's mind. Her hair hung in light angelic curls which framed her face perfectly, she wore a dark pea-coat that covered whatever she was wearing underneath, last her vixen red heals clicked against the tile sending a chill over Santana as she closed the door.

"Cash first." Brittany said coolly holding out her hand.

"Uh—there's an envelope on the bedside table. I can go get it upstairs if you-"

"That's fine." Brittany cut her off. Her eyes racked over Santana making her feel incredibly awkward about the whole thing. " There are a few rules before this happens. Rule one; what I say goes. If I say no or stop that means immediately. Two; I don't do kinks or fetishes. -"

"I—that's not really what I had in mind. Actually I was-"

"Rule three-" Brittany said louder. " This evening ends at 7:30 sharp. It's not negotiable. You have an hour and a half of my time. That's it. Four; after tonight you wont seek me out again. No texts, no phone calls, no nothing. Last are you the age of consent, because I'm not about to have sex with a minor and get sent to jail."

"I'm eighteen." Santana affirmed crossing her legs like a nervous school girl. There was something so intimidating about standing in Brittany's presence. She wondered what happened to the smiling happy stripper she met before.

"Perfect. So where do you want me?" Brittany asked unbuttoning her peacoat and dropping it to the floor.

"Oh god." Santana whimpered as she stared at Brittany. She wore a sheer red nightgown that only covered just past her naval and matching red lace panties which hooked onto two black garters that wrapped around her thighs. There was very little left to the imagination.

"M—my room is this way." Santana struggled to say practically tripping over herself as she turned around and headed up the stairs. Brittany followed with a lazy smirk.

She guided the woman through the long hallways until they reached her bedroom suite. Santana had made sure everything was cleaned twice before Brittany arrived.

"You c-can have a seat. Would you like some wine? I'll grab us some." Santana flushed darting out of the room to give herself a moment to breathe.

Five minutes later Santana returned with two glasses of wine and past one to Brittany who already had taken a seat on the bed. Her shoes were kicked off comfortably off to the side. She thanked Santana for the glass and took a sip while Santana sat next to her feeling awkward and shy. After another moment she turned to look at Brittany.

"You're really beautiful." She said softly hoping the woman would understand she was being sincere.

Brittany sat with her eyes focused and scrutinizing, as though she were trying to understand. With a small flick of her tongue the stripper took another sip of her wine and set it aside. Instead of replying she leaned forward and cupped Santana's face with her hand, placing a small peck on her lips. Santana felt her face grow hot, but she returned the small action.

Their kisses grew deeper with each turn they took until Santana felt as though she couldn't breathe properly. Brittany's hands cupped her neck pulling Santana in deeper and deeper. However Santana was at a total loss when it came to what she should do with her hands. She first thought to put it on the girl's hip, but then realized that might be too forward. For a moment she almost placed them on Brittany's chest, but that would be even more forward then having them on her hip. As a matter of fact it got so distracting that even Brittany noticed.

"What are you doing?" She husked with a slightly annoyed look on her face.

"I um-I'm not sure where to put my hands." Santana said sheepishly causing Brittany a great deal of confusion.

"Put them where ever you want. I don't care." Brittany ordered attaching her lips to Santana's neck. She could feel a rush of excitement in the pit of her belly with the new permission. Tentatively Santana slid her fingers along Brittany's stomach only to find rock hard muscle there.

"Fuck, your body is amazing." Santana whimpered as Brittany returned to her lips. She could feel her panties growing damper by the second. Her hand traced along the abs for a moment before she found the nerve to cup Brittany's breast in her palm. Brittany on the other hand felt no sense of restraint as she moved to straddle Santana's lap. Her pale hands make quick work sliding Santana's dress over her head and stripping off her bra, tossing it to the ground.

"Oh god..." Santana moaned and closed her eyes as Brittany licked one of her perky exposed nipples. Her hands flew to Brittany's hair on their own encouraging her to go on. Unfortunately just as the sensation started they stopped again.

"What's wrong with you?" Brittany asked flipping her blonde locks back out of her face.

"What—nothing. Nothing is wrong." Santana said sitting back on her hands to look at the sexy woman on her lap. Brittany however wasn't convinced.

"Look, I'm not into this whole virgin roleplay thing you've got going. That would fall under the kink category which I already made very clear to you. You're giving me $500 to fuck, so are we going to fuck or what?" Brittany asked impatiently.

Santana sank away from Brittany and looked away to hide her embarrassment. This night was quickly turning into a total disaster.

"Hold on, you're kidding right? I mean—you've done this before haven't you?" Brittany pressed. Some of the venom in her tone had vanished. Santana shook her head no, though she refused to look the stripper in the eyes.

"Are you a virgin?" Brittany hushed using her finger to draw Santana's watery eyes back to her own.

"I'm really sorry this was a stupid idea. When I saw you at the party I was too drunk to stand let alone think before I spoke. I never dreamed you would actually call back." Santana said hoarsely fighting back tears of embarrassment.

"Hey, come on. Don't cry. I hate it when girls cry. It's okay." Brittany shushed sliding off Santana's lap and kneeling down in front of her. "Don't you want your first time to be with someone you love?" She cooed.

Santana scoffed and rolled her eyes brushing away a tear and put on a strong face like a true Lopez.

"Like who? I'm a closeted lesbian who can only get respect by throwing money at people. Besides where am I going to find someone as hot as you?"

Brittany hung her head and sighed.

"You can go if you want. You can even keep the money." Santana stood and scooped up her little black dress tossing it into the hamper. She stepped over to her dresser and pulled on a batman sleep shirt since things weren't going where she had planned.

Brittany glanced at the clock and sucked in her bottom lip thinking the situation over.

"Alright look, the way I see it you've still got forty-five minutes,which is more than enough time for me to rock your world and teach you a thing or two about woman. You can sit there and pout about your sad little rich girl problems or you can take off everything you're wearing—including make up—and come lay down. " Brittany instructed.

Santana felt slightly dumb struck. Brittany still wanted to have sex even after everything that she had said?

"Forty minutes and counting."Brittany warned.

Santana wasn't about to waist anymore time then she already had, so she jumped up from the bed and dashed to her bathroom to change according to Brittany's orders. Two and a half minutes later Santana emerged from the bathroom stark naked. Every trace of makeup had been washed away.

"Wow, you actually look like a real person. I like it. Now come lay down." Brittany ordered and Santana obeyed.

Santana laid back on the fluffy dark pillows ,which matched her elegant looking room, and tried not to squirm too awkwardly or blush too much as Brittany hovered over her.

"Don't look so nervous. You're going to like this." Brittany teased settling herself down between Santana's leg. "The only thing you need to know is that this is supposed to feel good. If for whatever reason something I do doesn't feel good, just say so. But I've never had a complaint yet so no need to worry."

Brittany bent down and placed a series of soft kisses behind Santana's ear and down her neck. She trailed them across Santana's collar until working her way back to the younger girls lips.

"Do what I do." Brittany husked in Santana's mouth. She cupped Santana's breast, massaging it with her fingers. Santana waisted no time mimicking the action on Brittany's body. "Use both hands—good girl. Looks like you like it when I tell you what to do. I think we've just found a kink." Brittany smirked running her hands down Santana's thighs, forcing them upward to wrap around her back.

Brittany detached herself from Santana's swollen juicy lips and began kissing down between her breasts.

"Fuck. You're so good at this." Santana groaned as Brittany trailed steamy kisses over her belly. She could feel her core aching for attention. Her legs practically trembled. "I need you. I need this." Santana begged feeling Brittany's lips ghost over navel. Her hips bucked slightly of their own will.

"I'll fuck you when I'm ready and not before. Now stop talking." Brittany said placing her hand over Santana's mouth. After a moment she returned to her work, kissing every inch of Santana. This time it was the inside of her thighs, far from where Santana really wanted to feel her lips.

"You smell so sweet." Brittany husked placing a barely there kiss on Santana's core. "You're so wet too. I bet you love me telling you what to do because I'm the only one who's ever stood up to you." she used her tongue to take a long swipe at Santana. "Does it make you hot knowing that I'm holding all the cards?"

"Yes. Fuck. Please."Santana gasped. Her hands fell to Brittany's hair encouraging her to go on.

Not wanting to tease the poor girl any longer, Brittany buried her face well between Santana's legs, licking up ever once of arousal that came her way. The younger girl bucked and moaned enjoying every sensation that came with the feeling of Brittany's tongue on her. However despite the build up of pressure there was nothing that she would have referred to as "the big O".

Brittany sat back to catch her breath for a moment leaving Santana wondering if that was all there was. She dared not ask, but couldn't help the small feeling of let down she had. Not to mention she was still hornier then ever.

"Don't worry. That was just foreplay." Brittany grinned pulling Santana's body closer to her as if she could read her mind. Santana moaned again as Brittany bent down and kissed her fiercely. She could taste her own salty sweetness on the stripper's tongue, dousing her even more.

Santana gasped in surprise as Brittany's fingers slipped between their hot sweaty bodies and began tracing circles around her clit. Santana wrapped her arms around Brittany's neck desperate to hold on to something as the pressure began to quickly double.

"I'm going to fuck you now, babe." Brittany whispered in her ear as she moved her fingers lower, gently sliding two in as deep as they would go. "You okay?" She cooed softly pressing a series of softer kisses around Santana's brow.

"Yea...I'm good. Just a little tight." She panted back, her eyes practically rolling back in pleasure. Although the circumstances weren't normal, Santana felt like she had chosen the right person to give her virginity too.

Brittany giggled and placed a few more light kisses around Santana's face.

"That can be a good thing.." She murmured biting Santana's lip before kissing her longer and slower. As she did, Brittany slowly pulled her fingers out only to push them back in, this time moving them so the rubbed a sweet spot that Santana didn't even know she had.

"Shit." Santana gasped tossing her head back as Brittany repeated the action again several time. Each thrust had a little more speed and force behind it. Eventually Brittany worked her way up to a nice speed that rendered Santana unable to speak, with the exception of small gasps and moans.

"Fuck Britt, I -uhh-I can't take much more. I feel like I'm going to -ahh-explode." Santana whined arching her back off the bed as Brittany's long slender fingers pumped into her.

"So explode then." Brittany teased leaning down to suck the girl's clit, adding even more pressure. When she did it only too a moment more for Santana to go rigid.

She had never experienced something so intense yet also so blissful. It felt like all the muscles in her body had gone stiff with tension. Every nerve felt like fire, but in a way that was utterly delightful. She could barely control her body let alone the loud piercing sound that ripped from her throat. Then it was over.

Santana lay panting on her bed, her eyes half-open, and her mind sat in a dizzy haze. 'So that's what an orgasm feels like..' she thought.

"That was..."

"Shit...I've got to go." Brittany bolted out of the bed and quickly threw on her shoes.

"What! Why? " Santana sat up and looked over at the clock. It read 7:45. " Hang on, wait. You can stay for a moment or two off the clock. I can make you something to eat. No one is rushing you out."

"No, I'm already late." Brittany paused and looked over at a wounded looking Santana. "This was nice. I just have some place I have to be."

"Can I do anything to help?"

"No. I'm sorry." Brittany said truly apologetically. " Remember my rules okay?"

"I will, but Brittany I was wondering if you'd be interested in giving me lessons. You're amazing and I just want to be able to do what you do for someone else. -I don't mean to sound like a bitch, but I can pay for whatever time you're willing. I mean like actual lessons." Santana murmured shyly.

"I'll think about it, but wait for me to call you. Okay?" Brittany flipped her hair back and grabbed an envelope which sat on the bedside table. "Is this the cash?"

Santana gave a small nod before walking Brittany to the bedroom door.

"I can show myself out." Brittany said dismissively hurting Santana's pride. She took notice and quickly covered. " I'm sorry. You were really great and I had fun. Don't over think it okay?" She placed a sweet kiss on Santana's lips before rushing down the stairs and right out the door.

Santana sighed and closed her bedroom door. Tonight had been incredible, but now it felt more like a fading dream.

'I hope I see her again' She thought as she climbed back into bed and switched off the lights.


End file.
